Ergine
Encyclopedia
Ergine, also known as d-lysergic acid amide (LSA), d-lysergamide, and LA-111, is an alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

 of the ergoline
Ergoline
Ergoline is a chemical compound whose structural skeleton is contained in a diverse range of alkaloids including a few psychedelic drugs . Ergoline derivatives are used clinically for the purpose of vasoconstriction and in the treatment of migraines and Parkinson's disease...

 family that occurs in various species of vines of the Convolvulaceae
Convolvulaceae
Convolvulaceae, known commonly as the bindweed or morning glory family, are a group of about 60 genera and more than 1,650 species of mostly herbaceous vines, but also trees, shrubs and herbs.- Description :...

 and some species of fungi. As the dominant alkaloid in the hallucinogenic
Psychedelics, dissociatives and deliriants
This general group of pharmacological agents can be divided into three broad categories: psychedelics, dissociatives, and deliriants. These classes of psychoactive drugs have in common that they can cause subjective changes in perception, thought, emotion and consciousness...

 seeds of Rivea corymbosa
Rivea corymbosa
Turbina corymbosa Turbina corymbosa Turbina corymbosa ((syn. Rivea corymbosa), the Christmas vine, is a species of morning glory, native throughout Latin America from Mexico in the North to Peru in the South and widely naturalised elsewhere. It is a perennial climbing vine with white flowers, often...

 (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea tricolor
Ipomoea tricolor
Ipomoea tricolor is a species of morning glory native to the New World tropics, and widely cultivated and naturalised elsewhere. It is a herbaceous annual or perennial twining liana growing to 2-4 m tall. The leaves are spirally arranged, 3-7 cm long with a 1.5-6 cm long petiole...

 (morning glories, tlitliltzin), it is often stated that ergine and/or isoergine (its epimer
Epimer
In chemistry, epimers are diastereomers that differ in configuration of only one stereogenic center. Diastereomers are a class of stereoisomers that are non-superposable, non-mirror images of one another....

) is responsible for the psychedelic activity. In fact, the effects of synthetic LSA and iso-LSA are not particularly psychedelic, see Mixing the Kykeon below for a summary of human trials, and Chapter 17 and entry #26 of TiHKAL
TiHKAL
TiHKAL: The Continuation is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to PiHKAL: A Chemical Love Story, TiHKAL is an acronym that stands for Tryptamines I Have Known and Loved.-Content:TiHKAL, much like its...

 for further discussion. As a precursor to LSD
LSD
Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...

, ergine is a DEA
Drug Enforcement Administration
The Drug Enforcement Administration is a federal law enforcement agency under the United States Department of Justice, tasked with combating drug smuggling and use within the United States...

 schedule III drug
Controlled Substances Act
The Controlled Substances Act was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. The CSA is the federal U.S. drug policy under which the manufacture, importation, possession, use and distribution of certain...

 in the United States
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...

 and a Class A drug in the UK.

History

A traditional use of morning glory seeds by Mexican Native Americans was first described by Richard Schultes
Richard Evans Schultes
Richard Evans Schultes may be considered the father of modern ethnobotany, for his studies of indigenous peoples' uses of plants, including especially entheogenic or hallucinogenic plants , for his lifelong collaborations with chemists, and...

 in 1941 in a short report documenting their use going back to Aztec
Aztec
The Aztec people were certain ethnic groups of central Mexico, particularly those groups who spoke the Nahuatl language and who dominated large parts of Mesoamerica in the 14th, 15th and 16th centuries, a period referred to as the late post-classic period in Mesoamerican chronology.Aztec is the...

 times (cited in TiHKAL
TiHKAL
TiHKAL: The Continuation is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to PiHKAL: A Chemical Love Story, TiHKAL is an acronym that stands for Tryptamines I Have Known and Loved.-Content:TiHKAL, much like its...

 by Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...

). Further research was published in 1960, when Don Thomes MacDougall reported that the seeds of Ipomoea tricolor
Ipomoea tricolor
Ipomoea tricolor is a species of morning glory native to the New World tropics, and widely cultivated and naturalised elsewhere. It is a herbaceous annual or perennial twining liana growing to 2-4 m tall. The leaves are spirally arranged, 3-7 cm long with a 1.5-6 cm long petiole...

 were used as sacrament
Sacrament
A sacrament is a sacred rite recognized as of particular importance and significance. There are various views on the existence and meaning of such rites.-General definitions and terms:...

s by certain Zapotecs, sometimes in conjunction with the seeds of Rivea corymbosa
Rivea corymbosa
Turbina corymbosa Turbina corymbosa Turbina corymbosa ((syn. Rivea corymbosa), the Christmas vine, is a species of morning glory, native throughout Latin America from Mexico in the North to Peru in the South and widely naturalised elsewhere. It is a perennial climbing vine with white flowers, often...

, another species which has a similar chemical composition, with lysergol
Lysergol
Lysergol, is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi , and in the morning glory family of plants , including the hallucinogenic seeds of Rivea corymbosa , Argyreia nervosa and Ipomoea violacea. Lysergol is not a controlled substance in the USA...

 instead of ergometrine. Ergine was assayed for human activity by Albert Hofmann
Albert Hofmann
Albert Hofmann was a Swiss scientist known best for being the first person to synthesize, ingest and learn of the psychedelic effects of lysergic acid diethylamide . He authored more than 100 scientific articles and a number of books, including LSD: My Problem Child...

 in self-trials in 1947, well before it was known to be a natural compound. Intramuscular administration of a 500 microgram dose led to a tired, dreamy state, with an inability to maintain clear thoughts. After a short period of sleep the effects were gone, and normal baseline
Baseline (pharmacology)
In pharmacology and matters of biochemistry, baseline describes a person's state of mind or being with the absence of drugs. For example, after an LSD trip, baseline would be the point where the user is completely under control and no longer experiences any effects....

 was recovered within five hours.

In 1956 the Central Intelligence Agency
Central Intelligence Agency
The Central Intelligence Agency is a civilian intelligence agency of the United States government. It is an executive agency and reports directly to the Director of National Intelligence, responsible for providing national security intelligence assessment to senior United States policymakers...

 conducted research on the psychedelic properties of the ergine in the seeds of Rivea corymbosa, as Subproject 22
Subproject 22
Subproject 22 was a subproject of Project MKULTRA in which the CIA tested the effects of a plant known as Rivea corymbosa, a morning glory species containing the chemical LSA that has effects similar to those of LSD.-Purpose:...

 of MKULTRA.

Shamanic stories say ipomoea purpurea seeds, when swallowed or chewed, may incite a mild trip where synesthesia occurs and eye imagery is enhanced.

Natural occurrence

Ergine has been found in high concentrations of 20 µg/g dry weight in the grass Stipa robusta (sleepygrass) infected with an Acremonium
Acremonium
Acremonium is a genus of Fungi in the Hypocreaceae family; it was previously known as "Cephalosporium".-Description:Acremonium species are usually slow growing and are initially compact and moist. Acremonium hyphae are fine and hyaline and produce mostly simple phialides. Their conidia are usually...

 endophytic
Endophyte
An endophyte is an endosymbiont, often a bacterium or fungus, that lives within a plant for at least part of its life without causing apparent disease. Endophytes are ubiquitous and have been found in all the species of plants studied to date; however, most of these endophyte/plant relationships...

 fungus
Fungus
A fungus is a member of a large group of eukaryotic organisms that includes microorganisms such as yeasts and molds , as well as the more familiar mushrooms. These organisms are classified as a kingdom, Fungi, which is separate from plants, animals, and bacteria...

 together with other ergot alkaloids.

It is also found in the seeds of several varieties of Morning Glories
Morning glory
Morning glory is a common name for over 1,000 species of flowering plants in the family Convolvulaceae, whose current taxonomy and systematics is in flux...

 in concentrations of approximately 10 µg per seed, as well as Hawaiian Baby Woodrose
Hawaiian baby woodrose
Argyreia nervosa is a perennial climbing vine that is native to the Indian subcontinent and introduced to numerous areas worldwide, including Hawaii, Africa and the Caribbean. Though it can be invasive, it is often prized for its aesthetic value...

 seeds, at a concentration of around .3%.

Extraction

LSA can be extracted from morning glory (Ipomoea spp.
Ipomoea
Ipomoea is the largest genus in the flowering plant family Convolvulaceae, with over 500 species. Most of these are called "morning glories", but this can refer to related genera also. Those formerly separated in Calonyction are called "moonflowers"...

) seeds or Hawaiian baby woodrose
Hawaiian baby woodrose
Argyreia nervosa is a perennial climbing vine that is native to the Indian subcontinent and introduced to numerous areas worldwide, including Hawaii, Africa and the Caribbean. Though it can be invasive, it is often prized for its aesthetic value...

.

See also

  • List of Entheogens
  • Lysergic acid
    Lysergic acid
    Lysergic acid, also known as D-lysergic acid and -lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and some plants. Amides of lysergic acid, lysergamides, are widely used as pharmaceuticals and as psychedelic drugs...

  • List of psychedelic plants
  • Tlitliltzin (Ipomoea violacea)

External links

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